Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C

被引：20
|
作者：
Tian, Guilong [1 ]
Fedoseev, Pavel [1 ]
van der Eycken, Erik V. [1 ,2 ]
机构：
[1] Univ Leuven, KU Leuven, LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium
[2] Peoples Friendship Univ Russia, RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 22期
关键词：
2-aminoimidazoles; cascade reactions; guanidines; hypervalent iodine; kealiinine alkaloids; PSEUDOMONAS-AERUGINOSA; BIOFILM FORMATION; INHIBITORS; ANALOGS; CERATAMINE; ALKALOIDS; BINDING;
D O I：
10.1002/chem.201700934
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results.
引用
收藏
页码：5224 / 5227
页数：4
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